Cheap flights from Jamaica to Illinois from $233

The cheapest month to fly to Illinois from Jamaica is in December. Flight prices, which tend to average around $367, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of December, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $377.

The cheapest day to depart from Jamaica to Illinois is on a Tuesday when prices can be found for as low as $449. Flights from Jamaica to Illinois on a Sunday will generally be more expensive and average around $572. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from Jamaica to Illinois during this time can be as low as $476. Flights in the afternoon are often more expensive with an average ticket price of $486.

Fly from Montego Bay Sangster Intl to Chicago O'Hare Intl for the best Jamaica - Illinois flight prices

There are 2 cabin classes available to choose from on Jamaica to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 16% on your flight if you consider stops on a Jamaica to Illinois flight.

As of November 2026, 2 flights take off from Jamaica and land in Illinois each day. The most common flight departure time for this route is 2:00PM, with 100% of daily flights taking off in the afternoon.

The number of flights available between Jamaica and Illinois is 14 per week as of November 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.